Chicago is a major metropolitan city. It is expensive - in parts - and rough - in parts - not unlike LA, NY, SF, Tokyo, London, etcetera. Though unlike some of those other world class cities listed, Chicago provides amazing opportunities for experiencing a multitude of cultural and art events AT NO CHARGE to its residents. Yes the exchange is we all pay slightly more in taxes(+4%), but it helps to make Chicago world class.
Personally as a 28 year old male living with his girlfriend - full time school and work - I must say that Wicker Park/Bucktown has been amazing for the months we have lived here. The most amazing mix of old world Chicago families, hipsters, students, and young starter families as well.
Amazing nightlife, shopping, food, and downtown is five minutes by train if you need an expensive night out or world class shopping or to attend one of the many events.
Many neighborhoods in Chicago are distinctly segregated by class and/or race it seems from my exploring the city. Wicker Park, Bucktown, Ukranian Village, Logan Square, and more and more Pilsen seem to all eschew these lines. Though I'm not a hipster...they do seem to be the best barometer for a neighborhoods ability to meld cultures and often they are the first to venture outside established 'nice' areas.
Also check out the HotPads Chicago city page for area info.
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